Multi-step reaction with 12 steps
1.1: n-butyllithium / hexane; di-isopropyl ether / 0.5 h / -78 °C / Inert atmosphere
1.2: -78 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / toluene / 6 h / Reflux; Dean-Stark
3.1: n-butyllithium; N-cyclohexyl-cyclohexanamine / hexane; toluene / 0.08 h / 0 - 25 °C / Inert atmosphere
3.2: 1 h / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 25 °C
5.1: sodium hydride / tetrahydrofuran / 0.17 h / 25 °C / Inert atmosphere
5.2: 1 h / 80 °C / Inert atmosphere
6.1: toluene-4-sulfonic acid / acetone / 20 °C / Inert atmosphere
7.1: ammonium acetate / ethanol / 7 h / Reflux
8.1: 2,6-dimethylpyridine / dichloromethane / 10 h / 20 °C
9.1: Resolution of racemate
10.1: hydrogenchloride / ethyl acetate / 1 h
11.1: benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 20 °C / Inert atmosphere
11.2: 20 °C / Inert atmosphere
12.1: lithium hydroxide monohydrate / acetonitrile; water / 20 °C
With
2,6-dimethylpyridine; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; lithium hydroxide monohydrate; ammonium acetate; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; N-cyclohexyl-cyclohexanamine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; di-isopropyl ether; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;